Potassium Carbonate → 5-(2-methyl-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-one

HRID 542512Notes

Reaction equation

HRID 542512 reaction equation
Br[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:12])[NH:7]2.[CH3:13][C:14]1[NH:15][CH:16]=[CH:17][N:18]=1.CN1CCCC1=O.C(=O)([O-])[O-].[K+].[K+]>[Cu].C(O)(=O)C.O>[CH3:13][C:14]1[N:15]([C:2]2[N:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6](=[O:12])[NH:7]3)[CH:16]=[CH:17][N:18]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 127492-MethylimidazoleHCID 13387N-methyl-2-pyrrolidoneHCID 117758245-Bromo-1,6-naphthyridin-2(1H)-one

Product 1

HCID 100139235-(2-methyl-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-oneYield 42.6%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture containing 5.6 g of 5-bromo-1,6-naphthyridin-2(1H)-one, 8 g of 2-methyl-1H-imidazole, 25 ml of N-methylpyrrolidinone, 3.4 g of anhydrous potassium carbonate and 50 mg of copper powder was refluxed for 6 hours, allowed to cool to room temperature and then poured into 100 ml of water. The resulting solution was neutralized by adding acetic acid and the resulting solution was allowed to stand overnight at room temperature. The solid that separated was collected, recrystallized from dimethylformamide and dried in a vacuum oven at 90°-95° C. to yield 2.4 g of 5-(2-methyl-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-one, m.p. >310° C.

Workup

  1. temperaturewas refluxed for 6 hours
  2. customThe solid that separated
  3. customwas collected
  4. customrecrystallized from dimethylformamide
  5. customdried in a vacuum oven at 90°-95° C.

Sources & evidence

ORD record
ord-65cccba43bfb40fe83e9688528f493c5
Source dataset
uspto-grants-1987_04
Patent number
US04657915

Reaction notes

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